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The Total Synthesis of the Neurogenic Ganglioside LLG-3 Isolated from the Starfish Linckia laevigata

Authors

  • Hideki Tamai,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Dr. Hiromune Ando,

    Corresponding author
    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
    • Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Dr. Hide-Nori Tanaka,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Ritsuko Hosoda-Yabe,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Dr. Tomio Yabe,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Dr. Hideharu Ishida,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Dr. Makoto Kiso

    Corresponding author
    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
    • Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Part 152 of the series: Synthetic studies on sialoglycoconjugates. This work was financially supported by MEXT of Japan (WPI program and grant-in-aid for Scientific Research to M.K., No. 1701007 and No. 22380067). We thank Kiyoko Ito for technical assistance.

Abstract

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A gift from the star: The title compound, which was identified in starfish, contains two sialic acid units and was constructed utilizing a sialic acid derivative as a pivotal precursor. The potentially difficult conjugation of the phytoceramide portion with the glycan portion was achieved through the glucosyl ceramide cassette approach.

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